CN103342649A - 3-amino-2, 4, 6-trinitro-distyrene compounds and preparation method thereof - Google Patents
3-amino-2, 4, 6-trinitro-distyrene compounds and preparation method thereof Download PDFInfo
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Abstract
The invention discloses 3-amino-2,4,6-trinitro-distyrene novel compounds comprising substituents and a preparation method thereof. The structural characteristics of the compounds are as follows: two benzene rings are connected through a vinyl, wherein three nitro groups are located on positions 2, 4 and 6 of one benzene ring, an amino is located on position 3, and different substituents are connected to ortho-position and para-position of the other benzene ring. The 3-amino-2,4,6-trinitro-distyrene compounds can be potentially applied to the field of heat-resisting energy-containing materials.
Description
Technical field
The invention belongs to the energetic material field, be specifically related to a kind of substituent 3-amino-2,4 that contains, 6-trinitro-diphenylethylene compounds and preparation method thereof can potentially apply to heat-resisting energetic material field.
Background technology
The two keys that exist in the diphenylethylene compounds structure and the conjugative effect of phenyl ring make that such compound chemistry character is more stable.If introduce a plurality of nitros at phenyl ring, often can make the heat resistant type explosive of excellent property, as 2,2', 4,4', 6,6'-hexanitro-Stilbene, K.G.Shipp by the sixties in last century at first prepares by hypochlorite oxidation tritonal, and fusing point is applicable to-200 ℃ ~ 250 ℃ the gentle vacuum environment of height up to 317 ℃, blast performance and roadholding are all better, play a part very big in aerospace and subsurface investigation exploitation.Usually, have a plurality of nitros in the explosive molecule, this moment, amino introducing often raise owing to hydrogen bond action can make the fusing point of this compound or decomposition point, and system is more stable.True based on these researchs, amino is incorporated in many nitro toluylenes compound molecule will has potential value in heat-resisting energetic material field, both at home and abroad for the report of this respect seldom, so synthesize and novelly contain amino many nitro toluylenes compound and have great importance.
Summary of the invention
The objective of the invention is to synthesize a class and contain substituent 3-amino-2,4,6-trinitro-diphenylethylene new compound can potentially be applied to heat-resisting energetic material field.
3-amino-2,4,6-trinitro-diphenylethylene compounds is characterized in that having following structural formula:
Wherein work as R
1Be hydrogen, R
2Be methyl; Work as R
1Be hydrogen, R
2Be nitro; Work as R
1Be hydrogen, R
2Be chlorine; Work as R
1Be hydrogen, R
2Be bromine; Work as R
1Be chlorine, R
2Be hydrogen; Work as R
1Be chlorine, R
2Be chlorine.
3-amino-2,4, the preparation method of 6-trinitro-diphenylethylene compounds may further comprise the steps:
The first step, raw material 3-phenylmethylamine, Vinyl chloroformate, acid binding agent are joined in the reactor, methylene dichloride is made solvent and is reacted completely at normal temperature to reflux temperature, filter, filtrate is spin-dried for, gained liquid splashes in the mixed solution of nitrosonitric acid and the vitriol oil, temperature control is finished at stirring reaction below 0 ~ 55 ℃, adds water the mixed solvent with ethylene glycol then, and 70 ℃ to 100 ℃ reactions are finished, reaction solution is poured in the water, separate out yellow solid, filter, oven dry obtains 3-amino-2,4,6-trotyl.
Second step, with 3-amino-2,4,6-trotyl, contain substituent aromatic aldehyde, catalyzer joins in the reactor, in the reaction of benzene or reflux in toluene, after finishing, reaction boils off partial solvent, in reaction solution, drip organic alcohol to there being solid to separate out, filter, dry 3-amino-2,4,6-trinitro-diphenylethylene compounds.
Wherein, in the first step, the quality of nitrosonitric acid is 1.6 ~ 3.5 times of 3-phenylmethylamine quality, and the quality of the vitriol oil is 7 ~ 20 times of 3-phenylmethylamine quality.
In the first step, acid binding agent is selected yellow soda ash for use; It is ethylene glycol and the water of 3:1 that mixed solvent is selected volume ratio for use.
In second step, contain substituent aromatic aldehyde and select 4-tolyl aldehyde, 4-nitrobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehyde, 2-chlorobenzaldehyde, 2,4 dichloro benzene formaldehyde for use.
In second step, 3-amino-2, the feed ratio that contains substituent aromatic aldehyde are 0.5g:0.23 ~ 0.42g; Catalyst levels is 0.07g.
Preferred compound of the present invention is:
Be R
1Be chlorine, R
2Be chlorine.
Above-claimed cpd is 3-amino-2
', 4 '-two chloro-2,4,6-trinitro-toluylene, the preparation method may further comprise the steps:
The first step, raw material 3-phenylmethylamine, Vinyl chloroformate, acid binding agent are joined in the reactor, methylene dichloride is made solvent and is reacted completely at normal temperature to reflux temperature, filter, filtrate is spin-dried for, gained liquid splashes in the mixed solution of nitrosonitric acid and the vitriol oil, temperature control is finished at stirring reaction below 0 ~ 55 ℃, adds water the mixed solvent with ethylene glycol then, and 70 ℃ to 100 ℃ reactions are finished, reaction solution is poured in the water, separate out yellow solid, filter, oven dry obtains 3-amino-2,4,6-trotyl.
Second step is with 3-amino-2,2,4-dichlorobenzaldehyde, catalyzer join in the reactor, and back flow reaction in benzene or toluene solvant boils off partial solvent after reacting completely, in reaction solution, drip organic alcohol to there being solid to separate out, filter, dry 3-amino-2
', 4 '-two chloro-2,4,6-trinitro-toluylene.
The present invention compared with prior art, its remarkable advantage is: have following advantage after the preparation of 3-amino-2 that the first step of the present invention is related improves traditional synthetic method: (1)
NThe synthetic employing methylene dichloride of-(3-aminomethyl phenyl) urethanum is made solvent, has avoided traditional aromatic solvent; (2) 3-amino-2 synthetic with
N-(3-aminomethyl phenyl) urethanum is that raw material adopts the mode for the treatment of different things alike, and has avoided intermediate
NThe isolation and purification process of-(3-methyl-picryl) urethanum; The synthesis mode of (3) treating different things alike is compared the consumption that has significantly reduced sulfuric acid with traditional method, has reduced environmental pollution; (4) overall yield that makes 3-amino-2 of the method after improving by original be lower than 30% bring up to present more than 70%.
3-amino-2,4 involved in the present invention, 6-trinitro-diphenylethylene compounds can be used for heat-resisting energetic material field, and the heat resistant feature of this compounds is R
1, R
2All be chlorine atomic time fusing point up to 197 ° of C, all the other synthetic melting point substances all are higher than 220 ℃.Simultaneously, work as R
1, R
2When one of them or two were halogen atom (chlorine, bromine), the activity of carbon-halogen bond can make halogen atom quilt-OH ,-NO
2,-CN ,-N
3Replace Deng functional group, thereby synthesize the heat-resisting energetic material that has more potentiality.
Below in conjunction with accompanying drawing the present invention is described in further detail.
Description of drawings
Product 3-amino-4 in Fig. 1 example 1 of the present invention
'-methyl-2,4, the hydrogen nuclear magnetic resonance collection of illustrative plates of 6-trinitro-toluylene, X-coordinate is chemical shift.
Product 3-amino-4 in Fig. 2 example 2 of the present invention
'-nitro-2,4, the hydrogen nuclear magnetic resonance collection of illustrative plates of 6-trinitro-toluylene, X-coordinate is chemical shift.
Product 3-amino-4 in Fig. 3 example 1 of the present invention
'-methyl-2,4, the mass spectrum of 6-trinitro-toluylene.
Product 3-amino-4 in Fig. 4 example 2 of the present invention
'-nitro-2,4, the mass spectrum of 6-trinitro-toluylene.
Embodiment
The following examples can make those skilled in the art more fully understand the present invention.
Embodiment 1
3-amino-4
'-methyl-2,4, preparation and the sign of 6-trinitro-toluylene:
Structural formula:
Be R
1Be hydrogen, R
2Be methyl.
The first step: the preparation of 3-amino-2
With 3-phenylmethylamine (0.34 g), yellow soda ash (0.17 g), methylene dichloride (10 mL), Vinyl chloroformate (0.38g) joins reactor normal-temperature reaction 2 h, filter, filtrate is spin-dried for, the colourless liquid of gained joins in the mixed solution of nitrosonitric acid (0.54g) and the vitriol oil (2.38g), 0 ℃ is stirred 0.5 h, adding volume ratio then is the water of 1:3 and the mixed solvent of ethylene glycol (18 mL), after being warming up to 70 ℃ of reaction 7 h reaction solution is poured in the water, separate out yellow solid, filter, dry 0.54 g, overall yield is 70%.
Second step: 3-amino-4
'-methyl-2,4, preparation and the sign of 6-trinitro-toluylene
With 3-amino-2 (0.50g), 4-tolyl aldehyde (0.23g), benzene (15 mL), pyridine (0.07g) join and react 4 h in the reactor under reflux temperatures.Boil off partial solvent, drip ethanol to there being solid to separate out in reaction solution, cooling is placed, and filters, dry 0.63g, the orange crystal, 229 ° of C of fusing point, productive rate is 93.8%.
IR?(KBr):?ν=3456,?3352,?979?cm
-1，
1H?NMR?(500?MHz,?CDCl
3)?δ?(ppm):?9.560?(s,?1H),?7.383?(d,?J=8.5Hz,?2H),?7.331?(d,?J=16.5Hz,?1H),?7.213?(d,?J=8.0Hz,?2H),?6.693?(d,?J=16.5Hz,?1H),?2.385?(s,?3H)，MS：343?(M-1)。
3-amino-4
'-nitro-2,4, preparation and the sign of 6-trinitro-toluylene:
Structural formula:
Be R
1Be hydrogen, R
2Be nitro.
The first step: the preparation of 3-amino-2
With 3-phenylmethylamine (0.34 g), yellow soda ash (0.17 g), methylene dichloride (10 mL), Vinyl chloroformate (0.38g) joins reaction 2 h under the reactor reflux temperature, filter, filtrate is spin-dried for, the colourless liquid of gained joins in the mixed solution of nitric acid (0.76g) and sulfuric acid (3.76g), stirring at normal temperature 0.5 h, adding volume ratio then is the water of 1:3 and the mixed solvent of ethylene glycol (18 mL), after being warming up to 85 ℃ of reaction 7 h reaction solution is poured in the water, separate out yellow solid, filter, dry 0.55 g, overall yield is 71%.
Second step: 3-amino-4
'-nitro-2,4, preparation and the sign of 6-trinitro-toluylene:
With 3-amino-2 (0.50 g), 4-nitrobenzaldehyde (0.34 g), toluene (30 mL), sodium hydroxide (0.07g) join back flow reaction 14 h in the reactor.Boil off partial solvent, drip ethanol to there being solid to separate out in reaction solution, cooling is placed, and filters, dry 0.56 g yellow crystals, 220 ° of C of fusing point, productive rate is 72.3%.
IR?(KBr):?ν=3463,?3336,?970?cm
-1，
1H?NMR?(500?MHz,?CDCl
3)?δ?(ppm):?9.251?(s,?1H),?8.277?(d,?J=8.8Hz,?2H),?7.638?(d,?J=8.5Hz,?2H),?7.542?(d,?J=16.5,?1H),?6.696?(d,?J=16.5Hz,?1H)，MS：374?(M-1)。
3-amino-4
'-chloro-2,4, preparation and the sign of 6-trinitro-toluylene:
Structural formula:
Be R
1Be hydrogen, R
2Be chlorine.
The first step: the preparation of 3-amino-2
With 3-phenylmethylamine (0.34 g), yellow soda ash (0.17 g), methylene dichloride (10 mL), Vinyl chloroformate (0.38g) joins reactor and reacts 2 h down for 30 ℃, filter, filtrate is spin-dried for, the colourless liquid of gained joins in the mixed solution of nitric acid (0.76g) and sulfuric acid (4.59g), 30 ℃ are stirred 0.5 h, adding volume ratio then is the water of 1:3 and the mixed solvent of ethylene glycol (18 mL), after being warming up to 85 ℃ of reaction 7 h reaction solution is poured in the water, separate out yellow solid, filter, dry 0.57 g, overall yield is 74%.
Second step: 3-amino-4
'-chloro-2,4, preparation and the sign of 6-trinitro-toluylene
With 3-amino-2 (0.50g), benzene (30 mL), 4-chlorobenzaldehyde (0.32g), piperidines (0.07g) joins reactor, back flow reaction 5.5 h.Boil off partial solvent, drip methyl alcohol to there being solid to separate out in reaction solution, cooling is placed, and filters, dry the 0.68g yellow crystals, 232 ° of C of fusing point, productive rate is 90.7%.
IR(KBr):?3457,?3352,?972?cm
-1，
1H?NMR?(500?MHz,?CDCl
3)?δ?(ppm):?9.214?(s,?1H),?7.420?(d,?J=9Hz,?2H),?7.382?(d,?J=9Hz,?2H),?7.357?(d,?J=16.5Hz,?1H),?6.643?(d,?J=16.5Hz,?1H)，MS：363?(M-1)。
Embodiment 4
3-amino-4
'-bromo-2,4, preparation and the sign of 6-trinitro-toluylene:
Structural formula:
Be R
1Be hydrogen, R
2Be bromine.
The first step: the preparation of 3-amino-2
With 3-phenylmethylamine (0.34 g), yellow soda ash (0.17 g), methylene dichloride (10 mL), Vinyl chloroformate (0.38g) joins reactor normal-temperature reaction 2 h, filter, filtrate is spin-dried for, the colourless liquid of gained joins in the mixed solution of nitric acid (0.97g) and sulfuric acid (4.81g), 40 ℃ are stirred 0.5 h, adding volume ratio then is the water of 1:3 and the mixed solvent of ethylene glycol (18 mL), after being warming up to 95 ℃ of reaction 7 h reaction solution is poured in the water, separate out yellow solid, filter, dry 0.58 g, overall yield is 76%.
Second step: 3-amino-4
'-bromo-2,4, preparation and the sign of 6-trinitro-toluylene:
With 3-amino-2 (0.50 g), 4-bromobenzaldehyde (0.42 g) and piperidines (0.07 g), benzene (30 mL) joins back flow reaction 7.5 h in the reactor.Boil off partial solvent, drip ethanol to there being solid to separate out in reaction solution, cooling is placed, and filters, dry 0.70 g yellow crystals, 238 ℃ of fusing points, productive rate are 82.8%.
IR?(KBr):?ν=3456,?3352,?974?cm
-1，
1H?NMR?(500?MHz,?CDCl
3)?δ?(ppm):?9.214?(s,?1H),?7.539?(d,?J=8.5Hz,?2H),?7.368?(d,?J=16.5Hz,?1H),?7.349?(d,?J=8.5Hz,?2H),?6.624?(d,?J=16.5Hz,?1H)，MS：407?(M-1)。
Embodiment 5
3-amino-2
'-chloro-2,4, preparation and the sign of 6-trinitro-toluylene:
Structural formula:
Be R
1Be chlorine, R
2Be hydrogen.
The first step: the preparation of 3-amino-2
With 3-phenylmethylamine (0.34 g), yellow soda ash (0.17 g), methylene dichloride (10 mL), Vinyl chloroformate (0.38g) joins reaction 2 h under the reactor reflux temperature, filter, filtrate is spin-dried for, the colourless liquid of gained joins in the mixed solution of nitric acid (0.97g) and sulfuric acid (5.87g), 55 ℃ are stirred 0.5 h, adding volume ratio then is the water of 1:3 and the mixed solvent of ethylene glycol (18 mL), after being warming up to 100 ℃ of reaction 7 h reaction solution is poured in the water, separate out yellow solid, filter, dry 0.59 g, overall yield is 77%.
Second step: 3-amino-2
'-chloro-2,4, preparation and the sign of 6-trinitro-toluylene:
With 3-amino-2 (0.50 g), 2-chlorobenzaldehyde (0.32 g), toluene (30 mL) and pyridine (0.07 g) join back flow reaction 6 h in the reactor.Boil off partial solvent, drip ethanol to there being solid to separate out in reaction solution, cooling is placed, and filters, dry 0.69 g, yellow crystals, 223 ° of C of fusing point, productive rate is 92.1%.
IR(KBr):?ν=3452,?3344,?974?cm
-1，
1HNMR?(CDCl
3,?δ)?9.259?(s,?1H),?7.711?(dd,?J?=?7?Hz,?J?=?2Hz,?1H),?7.424?(dd,?J?=?7.5?Hz,?J?=?1.5?Hz,?1H),?7.385?(m,?3H),?7.089?(d,?J?=?16.5?Hz,?1H)，MS：363?(M-1)。
Embodiment 6
3-amino-2
', 4 '-two chloro-2,4, preparation and the sign of 6-trinitro-toluylene:
Structural formula:
Be R
1Be chlorine, R
2Be chlorine.
The first step: 3-amino-2 synthetic:
With 3-phenylmethylamine (0.34 g), yellow soda ash (0.17 g), 10 mL methylene dichloride, Vinyl chloroformate (0.38g) joins reactor normal-temperature reaction 2 h, filter, filtrate is spin-dried for, the colourless liquid of gained joins in the mixed solution of nitric acid (1.19g) and sulfuric acid (6.80g), 55 ℃ are stirred 0.5 h, adding volume ratio then is the water of 1:3 and the mixed solvent of ethylene glycol (18 mL), after being warming up to 100 ℃ of reaction 7 h reaction solution is poured in the water, separate out yellow solid, filter, dry 0.57 g, overall yield is 74%.
Second step: 3-amino-2
', 4 '-two chloro-2,4,6-trinitro-toluylene synthetic:
With toluene (15 mL), 3-amino-2 (0.50 g), 2,4 dichloro benzene formaldehyde (0.40 g) and yellow soda ash (0.07g) join back flow reaction 6 h in the reactor.Boil off partial solvent, drip ethanol to there being solid to separate out in reaction solution, cooling is placed, and filters, dry 0.71 g yellow crystals, 197 ° of C of fusing point, productive rate is 85.6%.
IR?(KBr):?ν=3458,?3353,?970?cm
-1，
1H?NMR?(500?MHz,?CDCl
3)?δ?(ppm):?9.218?(s,?1H),?7.551?(d,?J=2.5Hz,?1H),?7.484?(d,?J=8.5Hz,?1H),?7.373?(d,?J=16.5Hz,?1H),?7.320?(dd,?J=8.5Hz,?J=2.0Hz,?1H),?6.569?(d,?J=16.5Hz,?1H)，MS：397?(M-1)。
3-amino-2,4 involved in the present invention, 6-trinitro-diphenylethylene compounds can be used for heat-resisting energetic material field, and the heat resistant feature of this compounds is R
1, R
2All be chlorine atomic time fusing point up to 197 ° of C, all the other synthetic melting point substances all are higher than 220 ℃.Simultaneously, work as R
1, R
2When one of them or two were halogen atom (chlorine, bromine), the activity of carbon-halogen bond can make halogen atom quilt-OH ,-NO
2,-CN ,-N
3Replace Deng functional group, thereby synthesize the heat-resisting energetic material that has more potentiality.
Claims (7)
1.3-amino-2,4,6-trinitro-diphenylethylene compounds is characterized in that having following structural formula:
Wherein work as R
1Be hydrogen, R
2Be methyl; Work as R
1Be hydrogen, R
2Be nitro; Work as R
1Be hydrogen, R
2Be chlorine; Work as R
1Be hydrogen, R
2Be bromine; Work as R
1Be chlorine, R
2Be hydrogen; Work as R
1Be chlorine, R
2Be chlorine.
2. the preparation method of compound according to claim 1 is characterized in that this method may further comprise the steps:
The first step, 3-amino-2,4, the preparation of 6-trotyl: raw material 3-phenylmethylamine, Vinyl chloroformate, acid binding agent are joined in the reactor, methylene dichloride is made solvent and is reacted completely at normal temperature to reflux temperature, filters, and filtrate is spin-dried for, gained liquid splashes in the mixed solution of nitrosonitric acid and the vitriol oil, temperature control is finished at stirring reaction below 0 ~ 55 ℃, adds water the mixed solvent with ethylene glycol then, and 70 ℃ to 100 ℃ reactions are finished, reaction solution is poured in the water, separate out yellow solid, filter, oven dry obtains 3-amino-2,4,6-trotyl;
Second step, 3-amino-2,4, the preparation of 6-trinitro-diphenylethylene compounds: with 3-amino-2,4,6-trotyl, contain substituent aromatic aldehyde, catalyzer joins in the reactor, back flow reaction in benzene or toluene solvant, after reaction is finished, boil off partial solvent and in reaction solution, drip organic alcohol to there being solid to separate out, filter, dry 3-amino-2,4,6-trinitro-diphenylethylene compounds.
3. the preparation method of compound according to claim 2 is characterized in that: the quality of nitrosonitric acid is 1.6 ~ 3.5 times of 3-phenylmethylamine quality in the first step, and the quality of the vitriol oil is 7 ~ 20 times of 3-phenylmethylamine quality.
4. the preparation method of compound according to claim 2, it is characterized in that: acid binding agent is selected yellow soda ash for use in the first step; It is ethylene glycol and the water of 3:1 that mixed solvent is selected volume ratio for use.
5. the preparation method of compound according to claim 2 is characterized in that: in second step, contain substituent aromatic aldehyde and select 4-tolyl aldehyde, 4-nitrobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehyde, 2-chlorobenzaldehyde, 2,4 dichloro benzene formaldehyde for use.
6. the preparation method of compound according to claim 2 is characterized in that: in second step, urge agent to select sodium hydroxide, yellow soda ash, pyridine or piperidines for use; Organic alcohol is selected ethanol or methyl alcohol for use.
7. the preparation method of compound according to claim 2 is characterized in that: in second step, 3-amino-2, the feed ratio that contains substituent aromatic aldehyde are 0.5g:0.23 ~ 0.42g; Catalyst levels is 0.07g.
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| CN103910636B (en) * | 2014-04-03 | 2015-09-23 | 南京理工大学 | 2,4,6-trinitro--1,3-bis-(2 '-nitrostyrolene base) benzene, preparation and application thereof |
| CN104016868B (en) * | 2014-04-03 | 2016-03-02 | 南京理工大学 | 2,4,6-chloride trinitro--1,3-diphenylethyllene benzene derivatives, preparation and application thereof |
| CN103980131A (en) * | 2014-05-16 | 2014-08-13 | 南京理工大学 | 1,3,5-tri(3-amino-2,4,6-trinitro styryl) benzene compound and preparation method and application thereof |
| CN103980130A (en) * | 2014-05-16 | 2014-08-13 | 南京理工大学 | 1,4-di(3-amino-2,4,6-trinitrostyryl) benzene compound, and preparation method and application thereof |
| CN103992227A (en) * | 2014-05-16 | 2014-08-20 | 南京理工大学 | Energetic salt based on 2, 4, 6-trinitro-1, 3-di(2', 4', 6'-trinitro-3'-hydroxyl styryl) benzene, synthetic method and application thereof |
| CN104016869A (en) * | 2014-05-16 | 2014-09-03 | 南京理工大学 | 2,4,6-trinitro-1,3-di(2',4',6'-trinitro-3'-hydroxystyryl)benzene, synthetic method and applciation |
| CN104016869B (en) * | 2014-05-16 | 2016-01-20 | 南京理工大学 | 2,4,6-trinitro--1,3-bis-(2 ', 4 ', 6 '-trinitro--3 '-hydroxystyrene based) benzene, synthetic method and application |
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